After releasing three albums with the group, she broke up the band and embarked on a solo career. Her first solo album, Whatever, was a more introspective, folk-tinged effort than 'Til Tuesday's albums, and received uniformly positive reviews upon its release in the summer of 1993. However, the album was just a small hit, spending only seven weeks on the American charts, where it peaked at 127. Nevertheless, Whatever rejuvenated her career -- after its release, critics were praising her songwriting, as were peers like Elvis Costello, Difford & Tilbrook, and Andy Partridge.

Early in 1995, Mann had a modest hit with "That's Just What You Are," a song included on the soundtrack to the television series Melrose Place. Following the success of the single, Mann was set to release her second solo album in the spring of 1995, but her record label, Imago, filed for bankruptcy before its release. She signed a contract with Reprise Records after Imago went under, but Imago prevented her from releasing any records. For most of 1995, Mann battled Imago in an attempt to free herself from the label, eventually winning her independence at the end of the year. After her dispute with Imago was settled, she signed with DGC Records. Mann's second album, I'm with Stupid, was released in England in the late fall of 1995 and in January of 1996 in America. Again, it was greeted with positive reviews yet weak sales.

Mann's career got a kick-start in early 2000, however, when she released her soundtrack for the critically acclaimed film Magnolia; the song "Save Me" was later nominated for an Academy Award. Originally available only at live dates, the solo Bachelor No. 2 received national release in the spring. In the summer of 2002, Mann returned to the forefront with the self-released Lost in Space. Late 2004 saw the release of Live at St. Ann's Warehouse, a CD/DVD package recorded during her summer tour. It was followed in 2006 by the critically acclaimed Forgotten Arm, a concept album built around the return from Vietnam of a drug-addicted boxer. Mann released a collection of Christmas songs called One More Drifter in the Snow in 2006. @#%&! Smilers followed in 2008.

Mann spent the next few years working on adapting The Forgotten Arm into a musical, a project that was ultimately abandoned. She remained in the spotlight through semi-regular concerts and a memorable cameo on the IFC comedy series Portlandia before finally returning in the fall of 2012 with Charmer, her first album in four years. ~ Stephen Thomas Erlewine